My journey of leaving a dream job to pursue my passion (Part 1)

Also available on Medium.

January 15, 2018 will officially mark two years since I left a job that I loved at a company I loved working with people I loved, to go pursue a dream I’ve had for many years. Over the holidays I must’ve been sensing this milestone rapidly approaching, because I’ve spent a lot of time in thought, reflecting on this time and thinking about some of the seismic shifts I’ve made in my life since then. I want to share what I’ve learned with you during that time, however, before extracting lessons I think it’s important to set the proper context — as in, why did I leave a job that I loved at a company I loved working with people I loved in the first place?

Excellent question. In fact, it’s one I’ve asked myself under my breath several times over the toughest times this past couple of years, usually phrased along the lines of, “Matt, what the $*@# did you do??” While Zappos may not have been the highest paying job, lacking in politics, or devoid of workplace drama, it sure as heck was a better place to work than most. For a company their size, they still do a pretty good job hiring for culture-fit. Some of the most high-caliber humans I’ve met during my lifetime were my coworkers at Zappos. Zappos also does its damndest to truly make a workplace environment that is supportive, inclusive, nurturing, and fun. I genuinely looked forward to coming into work more days than not, which is saying something for a 5-year employee that spent a quarter of that time in customer service roles. The benefits package was bonkers (in a good way), and while I didn’t always see eye-to-eye with the CEO, I do not doubt his desire for building a company that truly transforms lives — even for those who aren’t employees or customers. So, why leave? It’s a complicated answer with a lot of factors, but the short version is that when the universe speaks, you listen.

The longer version:
If you read my Medium post in late 2015 entitled, “Thanks for All of Your Concern, but…” then you’re probably aware that in March of 2015, Tony Hsieh (Zappos CEO) sent out an email to all employees essentially mandating that either they get on board with where we were headed with our organization (one that was self-organized and moving towards a Teal model), or the company would pay them a generous severance- A month’s pay for each year someone had been at the company, with a minimum payout of three months — meaning if you’d been there for two years or less, you’d still get three months worth of pay. Pretty nice, right? Especially for people who had been with the company for over a decade, and there were several of them. It should also be noted that this was well over a year into our transition, so it’s not like this offer was “sprung” on anyone out of nowhere. It was simply a way to help people who were dragging their feet (or worse) give themselves permission to leave. After all, if all that’s keeping you at a job is inertia, you often end up harming the culture. 

Now, it was never my intent to actually take that offer. I loved the direction we were going — in fact, I was an internal coach and mentor helping others grow into that very framework. However, I had until December to make my decision, and frankly, having some insurance in case something changed between March and the end of the year felt pretty nice. Without getting too specific, over the summer months I felt that my ability to do my job and fight the battles that needed to be fought was becoming more and more restricted. So, that summer I decided that I would test the water and make my decision in October — either I would be all the way in and rededicated to Zappos or I would be completely out. I chose October so that if I did decide to leave, I’d have two months to work on transitioning my roles, training up replacements, and ramping myself down. During that summer, we had a ton of keynotes, presentations, and workshops being offered by people who were very intrigued by our transition to Holacracy and Teal and wanted to help us out. One of these was a Why Discovery Workshop, put on by Start With Why. I decided to take the full-day workshop, not necessarily because I wanted to “find my purpose,” but mostly out of a leadership development capacity. I had a bad habit of overextending myself (at the time I took the workshop, I held 25 separate roles, mapping to roughly 4 different titles) by chasing things I enjoyed, or things I was good at which I would be valuable to the org, or things that would give me good job security inevitably leading to me feel adrift/lost. I thought, “Well, if I’m going to be a leader in a self-managed ecosystem, I should probably learn more about myself, and what makes me tick.” Going through the workshop, for me, was transformative. It gave me insight into what truly gave me fulfillment from the work that I did, and gave me a filter for weeding out the things in my life that distracted me from it. I was so inspired, that I joined a group of about 10 other employees that met up with the Start With Why facilitators (unbeknownst to me at the time, one was the CEO) to discuss how we could bring this into our on-boarding process. After all, how awesome would it be for employees to come into self-management already knowing a clear direction for their own progression and growth? Start With Why was open to trying something new, and from that meeting stemmed their first Train-the-Trainer program. Soon after, a few of us began training to facilitate Why Discovery Workshops internally. Certification would be in two pieces — early and late October. (I know, right?!) Sign #1.

Over the next few months, in addition to my daily work, I trained for certification and I set up interviews with several start-ups and tech companies to gauge if there were better fits for me elsewhere. When October arrived, I went through certification prep training, and had a BLAST! I learned a lot, got critiqued even more, and felt like I would be truly making an impact with this work. This was a week of intensive, in-person training with David and Kim (the aforementioned facilitators). During one lunch, Kim — based in NY — overheard me talking with David — based in UT — about Green Chili, a food staple of my hometown/region. She asked me where I was from. I told her Pueblo West, CO. She laughed and said that she grew up about 40 minutes east of there, in Fowler. Now I laughed. She grew up in the same town where my parents grew up, the same town where my grandma still lives. After a brief exchange of last names, it turned out she knew my grandma and had met my sisters when they were in high school. Sign #2.

After that week of training was done, I took off the two weeks until final certification to clear my head and do interviews. After 10+ phone interviews and one physical visit, I decided that Zappos was still way better than a lot of other options, and I was actually happy where I was at. I was ready to recommit. The offer just wasn’t for a lifer like me. I went into final certification with a renewed sense of vigor. This must’ve bled into my facilitation that day because my certification went really well. However, we still had a ton of notes and feedback, so our debrief went late that night and I had to cancel my plans as a result. I asked everyone in the debrief room if they wanted to grab dinner, but my only takers were David and Kim. We went to my favorite Thai spot, a half block from my apartment at the time. As dinner began to wrap up, Kim casually said, “Dunsmoor, if you ever decide to leave Zappos, let us know.”

She paused.

“I want to be clear- I’m not saying that you should leave. We’re not out here poaching people, and we would never want that to be the perception,” she stated as if she could sense my giddiness. “I’m just saying that if you ever do leave, this is what we think you should be doing.” David nodded in agreement. Internally, I also nodded. Sign #3.

In that moment, I came to the conclusion that this was no longer chance. Rarely, if ever, in life do you get the chance to pursue your dream, do it with people who can help launch you on the right path, and have enough of a financial cushion to take a real shot at it, all at a time of your own choosing. I had to say yes or I’d regret it for the rest of my life.

Looking back, I’m 95% sure that when Kim told me to reach out if I left Zappos, she imagined me facilitating & developing for a couple more years at Zappos, then calling her up to say that I was ready for a transition. I’m 100% sure that she didn’t expect me to say, “Well, funny story…” that very moment. I told the two of them about my current situation and that, if they had a spot for me, I could start in January. Taken a bit aback, Kim and David told me they’d talk it over with the team and let me know. After an interview w/ two of the team members in CO during my trip home for Thanksgiving (one which came from my hometown, the other from my grandma’s town — Sign #∞), it was decided. I would contract with them as-needed beginning in January, and in the off-time I’d do my own thing- coaching, speaking, and consulting.

So, now you know! I still have a ton of respect and love for Zappos and the people working there. I have zero bad things to say about the organization. I just had a once-in-a-lifetime opportunity that I couldn’t walk away from. That’s why I took the leap. It’s a leap that has not always been the most convenient, positive, or fun. There have been a LOT of trials, fear/anxiety-inducing moments, and tough conversations, but it’s a leap that I’m eternally grateful for. In my time free falling since, a lot has changed and I’ve learned a lot from those changes. These learnings will be the topic of Part 2 😊